Sodium Iodide → 1,1,1,2,2-Pentafluoro-5-iodopentane

HRID 1267734Notes

Reaction equation

HRID 1267734 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH2:10][C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])(=O)=O>CC(C)=O>[I:1][CH2:8][CH2:9][CH2:10][C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 120170564,4,5,5,5-Pentafluoropentyl methanesulfonate

Product 1

HCID 120170571,1,1,2,2-Pentafluoro-5-iodopentaneYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (35.1 g, 2.15 mol) was added to a solution of 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (20 g, 0.781 mol) in acetone (200 ml), followed by heating under reflux for 12 hours. After the reaction mixture was filtered, the filtrate was concentrated. Ethyl acetate was added to the residue, which was then filtered again. The filtrate was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 1-iodo-4,4,5,5,5-pentafluoropentane (21.1 g, Yield 93.4%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 12 hours
  3. filtrationAfter the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. additionEthyl acetate was added to the residue, which
  6. filtrationwas then filtered again
  7. washThe filtrate was washed with water and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-848ca61def214993b4660013c784b2c8
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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